


Men In Drag

by Geli



Category: The Sentinel
Genre: Drag, Humor, M/M
Language: English
Status: Completed
Published: 2013-05-10
Updated: 2013-05-10
Packaged: 2017-12-11 04:15:47
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,337
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/793861
Author URL: https://archiveofourown.org/users/Geli/pseuds/Geli
Summary: <blockquote class="userstuff">
              <p>Blair hears about Jim in drag undercover, and Jim dares Blair to try it too.</p>
            </blockquote>





	Men In Drag

**Author's Note:**

> Well, in Germany we have Carnival and men in drag is definitely a classic here. I've seen a lot of men in drag in my life, straight, bi, tri, whatever you want. Including male friends and family members. It's always a lot of fun.  
> This isn't a wimpy Blair/ butch Jim story. It's more a battle with uncomfortable clothes story.  
> I have to thank Moonshadow for betareading.  
> Too bad that there is no Carnival in USA, it would make so many funny stories.  
> Have fun.

The loft, 8.18 p.m. The two guys were watching television after a long day.  
The program wasn't very interesting so Blair started to study his friend instead. Suddenly he snickered. Jim looked up, just wanting to take a swig of his beer. He saw that Blair was laughing at him. 

"What's so funny Sandburg?" He said, annoyed. 

"I was wondering how you'd look in a dress." Blair explained, grinning. 

Jim's eyes went round. 

"Awful! I can promise you that." He took a quick swig of beer. "What the... where the heck did this come from? Is this a new kink? Muscular guys in drag?" 

Blair laughed. 

"Nah. Today a friend of mine showed me a book about the history of female impersonations. 'The Great Pretenders'. With lots of pics. Now I can't help myself but wonder what my male friends might look like, you know, like that." 

Blair cupped his hands in front of his chest. Jim shook his head, but Blair rambled on. 

"Do you know where drag queens came from? They were with minstrel shows and...." 

"Fascinating, Sandburg, but I'd really just like to watch the show." Jim interrupted him. 

Blair was quiet for about 20 seconds - a new record. He was really learning patience living with Jim. 

"Have you ever been dressed up as a woman?" 

Jim opened his mouth to order Blair to be quiet when his brain registered the question. 

"No!" 

*Shit!* He had answered a little too quickly. *Kid's gonna be all over me about this!* 

Blair scooted closer with gleaming eyes. 

"Tell me about it. Was it in Vice? Undercover, right? Do you have pictures?" 

Jim silently implored the gods for a distraction. Anything. A serial killer, a bomb, a sudden outbreak of anthrax, ANYTHING. No such luck. He sighed. 

"Was it that bad? The high heels killed you? Right?" Blair looked sincere. 

"Yeah. I almost broke my neck when I had to fight and run in those damn shoes." 

Blair was now practically sitting on his lap. Jim felt suddenly pride when he remembered how he'd survived the ordeal. 

"Okay, you wanna hear the whole story? Okay, fine. We were trying to catch this perp. The new faces on the force had to go undercover and watch the streets. I ended in this mini mini-skirt and high heels." Jim held his hand up and spread his thump and index finger to indicate how high. "I tore the tights immediately. The whole get-up looked awful. I had this big, blond wig. They plastered layers of makeup on me and gave me these big boobs. Only a half-blind man would have mistaken me for a woman." Jim sighed again. 

"Wow, that must have been awful. I once tried to walk in my girlfriend's high heels and I sprained my ankle. So, got any pictures of this...incident? " Blair asked hopefully. 

Jim searched Blair's face for a moment before he made a decision. He went up to his bedroom and came back with three photographs. Two showed him standing in the street with other cops in drag. One was with him alone in a close-up shot. Blair got his glasses and studied them. A slightly younger Ellison laughed shyly in front of the camera. The long legs looked great, but the bulging biceps and the muscular neck was so male. Blair smiled. 

"What?" Jim asked. 

Blair grasped Jim's upper arm. "Nice face and legs, but too much of that!" 

Jim grinned and pouted. "So that's what you think of my impersonation, nice legs. What about you? If you got rid of your sideburns and chest hair, you'd make a half-decent looking woman." With that he tucked at some strands peeking out Blair's shirt. Blair batted his hand away. "I might even ask you out." 

Blair made a dramatic face. "So you would only date me if I were female. How sexist of you." He chuckled. "That's discrimination! I didn't ask to be a man!" 

"I didn't mean it like that. I meant... I think... If you were a woman you would like men, right? So we could date." Jim thought it didn't sound as logical as he meant it. 

Blair shook his head. "What if I were a lesbian." 

Jim frowned. "So if you were a woman you'd be a lesbian? If I were a woman I would still like men." 

Blair blinked at him. He wasn't sure he had heard what he thought. Jim stared at the pictures in his hands. 

"No. I think I would be bi. I like men and women." Blair said calmly. 

Jim looked up in the eyes of his friend and smiled softly. "Me too." 

Blair snuggled closer, threw his head back and asked: "So, would you like to see me in drag?" 

Jim studied his hairy partner. "Ahem. I'm _not_ sure about it. Unless I can undress you afterwards." 

"Done!" 

They sat a while, their comfortable rapport suddenly grown quiet and shy as they contemplated this new development and found themselves unsure how to proceed. Blair studied Jim's clothes in the photograph. His skirt was a black micromini that looked smaller than the boxers Jim wore know. 

"Was the skirt made of rubber?" 

"Yeah. They wanted me to wear a rubber shirt too. But I refused." 

Blair studied the picture again. Jim wore black tights, black shoes and a flaming pink and blue Hawaiian shirt which was knotted between the large fake breasts, leaving Jim's washboard stomach free. A large Farrah Fawcett wig cascading down Jim's back. Gaudy jewelry completed the picture. On closer inspection, Blair noticed the hair on Jim's forearms was gone. 

"Where did you hide your weapon?" It was all so tight, Blair thought. 

"Uhm. I had a small gun - a .22 caliber - over my heart. You know, back then I thought 'For this I went to the academy?'" 

They laughed. Suddenly Blair realized he wanted to hear the end of the story. 

"This perp you wanted to catch, what had he done?" 

"He'd beaten up the male hookers and raped them. Actually they were two, we found out later. They drugged their victims with ether and dragged them in a van. Later, they threw them out somewhere outside Cascade. They only went after young and weaker men. Of course, we didn't know that so we weren't exactly useful as bait." Jim held up the photograph showing a bunch of athletic, tall men. 

Blair laughed. "I think a man would need guts to ask someone like you for a trick." 

"I looked frightening. I would have been scared if had had to date myself. Anyway, we were ordered just to keep a lookout, observe the traffic on the strip. We had to blend in and keep a low profile. The other hookers knew about us and tolerated us. There was this older guy, probably 50 or so, who was a kind of a mom out there. He tried to teach me how to strut. He kept telling me if I didn't learn to shake it, I'd never have a career. He kept it up even after he found out I was a cop. He was adamant, he wanted to train me properly, because the job is more than just sex." 

"Oh man, I think I would love to see you to be trained." Blair clutched at a cushion so tightly he was afraid it would burst. 

"I've asked him if he could still make money at his age, you know, get clients. 'Oh, you'd be surprised' he explained to me." Jim made some flamboyant, effeminate movements imitating the aging hustler. "'There are men who prefer experience over beauty. Besides many of them are just lonely. They want some nice company and someone who listens, sweetie." 

"What happened to him?" 

"He retired and went to Florida. I bet he tricks, just to keep in practice." 

"Were you in a relationship back then?" 

"Yeah, she was the one who took the photographs. She laughed the whole time." Jim grinned. Blair grinned back. 

"Did you get many offers?" 

"Some. I was too intimidating, I think. I gave off this heavy military 'don't screw with me' vibe." Blair smirked, Jim ignored it.  
"But there was this one guy who came around at least four times a day to ask me. I always told him I was waiting for my date to pick me up and sent him away. In the end, I told him I was cop but it didn't deter him. He wanted to 'invite me for a drink' after work." 

"Did you see him again?" 

"Yeah. He was a friend of Caroline's family. He recognized me when we met again at a party at her parent's home. He turned purple. Really." 

"How did you get the perp?" Blair leaned forward entranced by Jim's story. 

"Jeff spotted him first. We followed him. He noticed us and started to run. Micki saw him coming and jumped at him. We threw ourselves on him and flattened him on the pavement. It was a primitive tactic," Jim laughed," but we didn't want to risk a real fight in our outfits. His buddy was waiting at home. He sang like a canary." 

Jim gazed down at his grinning friend. "So have you ever worn drag?" 

"No. Not really. I had once a girlfriend who had me wear her sexy underwear before she pounced and ravished me. I liked that." Both men laughed. 

"You want me to pounce and ravish you?" Jim asked teasing. 

"Nah! I'll do that with you!" 

Jim sobered. There was a calculating gleam in Blair's eyes, one that belied the innocent face of a scholar behind owlish glasses. Jim had the weird vision that he was dealing with a wolf in sheep's clothing. While he, on the other hand, felt like a kitten pretending to be a big panther. 

Jim paused and listened to a distant sound beyond loft's door. "It's time. I have to go, Brown is waiting." 

"When will you be back?" 

"Around 6 am, I think." 

When Jim walked out the door, he turned and gave Blair a kiss on the cheek. Blair blushed and Jim found it adorable. His friend, Mr. Casanova Lady-Killer Don Juan, was blushing like a teenager. 

Blair made himself comfortable on the couch and started to surf channels, but his thoughts were still lingering over Jim. His friend wanted to undress him. Oh, yeah! Slowly and lovingly, layer by layer. He was sure Jim was a sweet lover, if the gentleness he showed towards children and animals was any indication. After watching a documentary about perception and reality he went to bed. 

At 3 am, Blair felt someone nudging him to roll over. Jim got into bed and shivered beside him, cold as ice. 

"We spent half the night searching the park", Jim whispered, "chasing the idiot." 

"Mmmh, slmm." Blair mumbled, turning and wrapping himself around Jim. 

* * *

Several weeks later 

When Blair heard Simon's voice at the front door, he practically leaped into his room and locked the doors behind him. Jim and Simon walked in. The loft smelled different. Jim knew Blair was here, but he was hiding in his room. Something was cooking at the stove. Simon got himself a beer from the fridge. 

"Where's Blair?" He asked Jim. 

"Don't know." Jim went into the bathroom. Makeup cluttered the sink and several of the shelves. Realization hit Jim. Blair was in drag! He backed out of the bathroom, made up a lie about having a headache and saw Simon to the door. 

"Blair you can come out. Simon is gone." 

Blair stepped hesitantly out of his room, a shy smile on his face. He looked...strange. 

He wore a long flowing silver evening dress. It had a high bodice and looked like something Jane Harlow might have worn in the thirties. His sideburns and the chest hair were gone. He had a perfect makeup job and something fantastic had happened to his hair. Jim doubted that Blair could have done this all himself. He was really beautiful. If there weren't for the broad shoulders and hands and the Adam's apple, Blair could have passed as a woman. Blair made some small, elegant steps toward Jim, swaying his hips with each step. 

"Hi babe, how about a shower. I'll prepare dinner." 

Jim obediently went for his shower though he shook his head in bemusement. When he had dared Blair to wear drag, he hadn't thought his lover would go so far. He just had wanted to find out if the kid had the nerve to actually do it. 

When Jim came out of the bathroom, he sat down at the kitchen table clad only in his robe. He could only stare at the vision puttering around the kitchen. The tight dress and the high heels forced Blair to move carefully. It was very un-Blair-like. But he obviously was having fun trying to work in the unfamiliar clothes. He overdid the tripping around when he noticed Jim's amused expression. Blair set the table and served the meal before planting himself on Jim's lap. He had outdone himself with an excellent meal. Soft music played in the background. 

"Can I kiss you? Or would I ruin everything?" Jim asked smiling. 

"Don't panic. It's action make up. Kiss me, stupid!" 

Jim obliged. When he closed his eyes, there was only his old Blair in his arms overlaid with the strong smell of cosmetics. He opened his eyes again there sat this strange, beautiful person on his lap. 

"Who did all this to you?" He asked. 

The curls had been drawn out and piled in a extravagant waves around the younger man's head. Jim carefully touched Blair's hair. It almost felt solid with so much hair spray on it. 

"A friend of mine. She is a makeup artist in the theater department at Rainier." 

"I see." 

"I tried to do it myself. It was a disaster, I looked like a scarecrow. So asked her for advice. She offered to come over and do it herself." 

"What did you tell her about it?" 

"I told her it was a bet. Man, imagine what Simon would have said if he had seen me like this?" 

"He would have revoked your observer status immediately. Although I seem to remember he's been in drag undercover too." 

"Simon? Our Simon?" Blair couldn't believe it. "Give me another kiss and I'll feed you." 

Jim kissed him thoroughly and Blair fed him in between tiny bits and kisses. Sated, Jim stood up and led Blair into the living room.  
"May I?" He embraced Blair gently and they danced slowly together. The neighbors from the other side of the street would get an eyeful. Softly swinging to the music, they clung at each other. It was quite a picture - Jim wearing only his old gray robe and no shoes and Blair dressed up like a vamp. His three inch high heels made kissing a lot easier. After a while, Jim decided it was time to do something about their increasingly obvious erections. 

He dragged his lover upstairs and sat on the bed. Blair stood in front of him. Slowly, tantalizingly, he led glide the wearer down and slid down the zipper on the gown. The dress fell from his shoulders and pooled at his feet. Blair stepped out of his dress and stood in front of Jim, hands on his hips, daring him to laugh. Jim's eyes almost popped out. He wore a small corset and a suspender which held the black stockings. It was pink with lots of lace. 

"Wow! Where did you get all this stuff? Don't tell me you went in a shop and tried it on." 

Blair grinned and turned around to give Jim a better view from all angles. He pulled the rubber breasts out of the corset and flung them away.  
Jim had to laugh because Blair had only shaved that part of his chest that wouldn't be covered by his dress. The dark hair still covered his belly and ended in his pubic hair which peeked out of the tiny panties that barely keeping his assets inside. His cock had already freed itself and stood stiffly poking through the leg of delicate underwear. 

Jim almost strained something trying not to laugh out loud. Blair looked like a conglomeration of male and female depending which body part he looked at. 

Blair got annoyed. Jim was laughing at him. He'd endured hours of torture and his idiot of lover laughed! Well, he needed a lesson! 

He shoved his panties down and crawled on the bed between Jim's spread legs. He snatched a hand and wrapped the panties around the wrist. Jim grinned, before he knew what had happened the other hand was also wrapped and tied to the railing. Jim chuckled and tugged at the impromptu binding. It held and he shot a surprised look at Blair.  
Blair only shrugged. 

"You know Jim, I think it's time you learn who's in charge around here. And the best way to learn is for you to be the bottom." 

Jim wiggled nervously. They hadn't done that before. Blair had let him take it slow since he was a bit of a newbie to the whole male/male thing. Jim ventured a shaky smile designed to soothe his lover while tugging at his ties again. Jim was sure Blair wouldn't really hurt him but some part of him was a little bit intimidated by the bossy behavior. He couldn't figure out how to get out of this situation without begging or attacking Blair. 

Blair fondled the bound Sentinel's hard pecs and sucked at his nipples. Jim threw his head back and moaned helplessly. His senses were fully aroused and had made him a lot more sensitive to the slightest caress. He felt like he was going to explode. 

When Blair noticed Jim's nipples couldn't take anymore, he nipped down the hard stomach to his attention-starved erection. Jim was already rock hard and leaking. Blair took the head in his mouth and suckled. He ran his tongue along the underside. That always made Jim crazy. Jim was reduced to emitting guttural sounds as his body became taught with increasing tension. Blair smiled around the large cock and redoubled his efforts. Jim came off the bed with a shout as his orgasm surged through him. 

Blair rubbed the spilled seed over Jim's opening. Breathing hard, Jim watched Blair getting himself and Jim ready with lube and condoms. Jim felt like a wet towel. Blair had purposely brought him off fast so that Jim couldn't offer any resistance. Jim silently congratulated Blair on his sneak attack tactic. 

Blair moved Jim's relaxed limbs to accommodate the next stage, carefully probing Jim's hole with his finger. 

"You are still not relaxed enough!" Blair scolded him. 

Jim made a guilty face and tried to relax more. Blair wasn't satisfied and started to tickle him all over. Jim laughed and tried to doubled up. 

'This is it!' Blair thought and sat firmly on Jim's legs and let his fingertips just slide over the big man's ribs. Jim howled and twisted forcefully. Blair knew all best places. Suddenly Jim's wailing became a scream. Blair jumped and pressed his hand over Jim's mouth. 

"Are you crazy? The neighbors are gonna call the cops!" 

Jim desperately tried to get air through his nose. He was panting heavily and his whole body shook. Blair let his hand go. 

Jim took a deep breath and hissed: "Shit! Are you trying to kill me?" 

"Nah, you're more useful to me alive." 

Jim glared at him. "I've fallen into the hands of a madman!" 

"Madwoman," Blair corrected him. "The female side, that's my dark side, you know! Can you hear if some one is calling the police?" 

Jim listened intently. "No, nobody." 

"Okay then, let's get back to it." 

If there was one thing that Jim really admired in Blair it was his ability to concentrate on whatever interested him, no matter the distractions. 

Blair began to stretch him carefully. 

"Can't you untie me?" Jim almost whined. 

"No, no chance, I want to pound you into next week and I'm afraid I'll shove you right off the bed and down onto the kitchen table. You know, like you do all the time with the pillows. We need a headboard, man! Before one of us lands head first down there." 

Once he had loosened up Jim enough, Blair knelled in front of him and hoisted the long legs over his shoulder. He was ready, condom and all, he only needed Jim's okay. 

"Do it! Make me! Make me scream, the neighbors don't care anyway." 

With a single thrust, Blair shoved in and Jim cursed expressively. After a moment of adjusting, Blair began to fuck him hard. Jim bawled and squirmed under him. He felt like a hammock stretched between the railing and Blair's cock. The whole bed shook. Jim's penis was suddenly hard again. Blair pumped him with one hand while the other grasped for something to hold on to. Jim screamed as if he were riding a hurricane. The mad dance ended in a double explosion. 

Blair collapsed onto him. 

"Hey!" Jim blew cold air in his face. "Untie me!" 

Blair stared at him for a moment before he reached up and freed Jim. His wrists were red and had marks. 

"What about the condom?" 

Blair's hand slid down to remove the spent rubber which he threw in general direction of the wastebasket. Then he was out cold. Jim embraced him and covered them both with the comforter. He kissed him gently and fell asleep too. 

Jim awoke to the feeling of something strange on his face. It took him a minute to realize it was the mop of Blair's hair , still stiff from the hairspray. Jim studied his lover. He was a mess. The makeup was smeared. The thick black rings under his eyes from the dyed eyelashes and the heavy beard shadow gave him a grotesque look.  
Jim smiled - war paint after battle. 

Jim thoughtfully traced Blair's stocking-clad leg. It felt silken and warm. He turned around and snuggled against the legs and stroked them up and down. He pulled Blair's feet up until they were tucked under his chin. 

Blair woke up to a tickling sensation. He opened his eyes and found his lover dreamingly playing with his legs. He closed his eyes, relaxed and let the sensation wash over him. And fell asleep again. 

Two hours later they awoke. Blair had shoved his foot into Jim's face. Jim rubbed his nose, annoyed. 

"Nobody told you to sleep on my feet! I need a shower." Blair declared. 

He was grouchy and with a frown he climbed over Jim who tried to get out of his way. 

"Ouch! Shit, I'm sore!" Jim grimaced. 

Carefully he moved to find a comfortable position for his butt. The welts on his wrist were still red and tender. Blair went down the stairs towards the bathroom. Jim turned the TV on and surfed channels and settled briefly on a women's golf championship, live from Scotland. 

Then he heard the horrified cry from the bathroom. Blair had seen himself in the mirror. Jim grinned and snuggled under the covers. 

Almost an hour later the old Blair brought up coffee for them and joined Jim. Aside from the great, mind-blowing sex, he had suffered a lot for this. While struggling to rid his skin of the smeared makeup, he had decided that Jim should suffer, too. 

"So, Jim babe, now it's your turn!" 

Jim played dumb. "Whaddya mean 'my turn'?" 

"It's your turn to dress up. Stockings, makeup, wig, the whole get-up! I like my women in stockings - black with a line up the back. I know where I could get you high heels. Like the ones from the fifties." 

"You want me to break my legs so that you can keep me in bed all the time and fuck me." 

"Hold that thought - I might get back to it! Anyway, you don't need to walk around. Just stand, posing and I'll stare at you for hours." 

Jim smirked. "That's bullshit, you'd jump me after 5 minutes." 

"And I want a wig like that one in the picture but with you own hair color." 

"Unh-unh, no way, they itch! I'll dye my hair and do Annie Lennox." 

"Who?" 

"Eurythmics!" 

Blair looked critically at Jim. "But I want to see you with long hair." 

Jim sighed and rolled his eyes. He thought he looked silly in with long hair. And having long hair, even temporarily, only made him more self-conscious about his increasingly thinning hair. 

"What if the dye can't be removed? I can just see it now - Ellison with red hair in the bullpen." 

"I can shave it off." 

"Yul Brynner!" Blair made a face. 

"Nah, Kojak!" 

"Leave it and say it was a bet, like George Clooney with his hair dyed blond." 

"As if anybody would believe that." Jim snorted. 

"So? Use a wig! I know how messy dye can be." 

"Speaking from experience, Mata Hari?" 

"Nah, I had this girlfriend who dyed her hair with all kinds of strange colors." 

"Well, I've had enough of this drag thing for a while. Next year maybe." 

"Next year? No way! Next month! Or I go on strike!" 

"What kind of strike?" Jim asked, suspicious. 

"Well, my bed is still downstairs." 

"You are blackmailing me with sex?" Jim laughed. 

Blair made a stubborn face but he knew who was the ascetic in their relationship. He could hibernate alone in his bedroom, Jim was stronger than him in this contest. 

"What do you want?" Blair asked trying a different approach. 

"I want you to help me, I can't do that alone and," forestalling Blair's excitement, "I don't want that theater friend of yours to see me like this." 

"Done!" Blair kissed Jim tenderly and snuggled close. He was already starting to make plans. 

The end. 


End file.
